Pepperwood's Nighttime Adventures
by mochocolate
Summary: Jess sneaks a peek at Nick's latest chapter, and is shocked at the change in genre.
1. Chapter 1

It was a sunny, quiet day in the loft. Winston was sleeping on his adjusted schedule, and Schmidt was at work. Unfortunately Nick was also out somewhere, and Jess needed to transfer a file that she'd started working on on his computer.

It'd be silly to wait, she thought to herself, not even sure if he was coming home soon or if he was working until late. So she clicked open his door and made herself comfortable at his desk, prying open his laptop.

She sat absentmindedly enjoying the quiet of his room. When his computer finally booted up, she opened his word processor and started looking for her file.

Something caught her eye.

The filename tempted her from the top of his list of recent files. Jess felt a rush of excitement and pride when she realized that Nick had made some progress on his novel. Should I? She thought to herself, but her finger had already clicked Open, and she told herself she would just peek ahead and see what he had written.

The page filled the screen and, feeling just a little bit like she was doing something bad, she started to take it all in.

Pepperwood's Nighttime Adventures

_It was dark, real dark, the kinda night where you couldn't see your own hand in front of your face, even if you had a shiny ring on. The summer air was hot and heavy. Julius Pepperwood, zombie detective, halted at the entrance to his office. Through the window above the door he could see that a light was on inside. He wasn't expecting any visitors. He'd sent his sidekick, Jessica Night, home earlier in the day. The heat was taking a lot out of them. Frowning, he placed one hand on the gun at his side as he opened the door. His heart was pounding like a kick drum in his chest. Julius Pepperwood was tough, real tough, out there on the streets. But the thought of danger coming to find him in his office spooked him a little._

Jessica paused, enjoying the mood Nick had set at the beginning of this chapter, though she was disappointed to see that she wouldn't be included in the night's adventures.

She flicked her eyes down to the next paragraph.

_The sight in front of him didn't do anything to slow his heartbeat. His assistant was standing up high on his desk, reaching above her head for some old case law volumes he kept out of the way in the bookshelves. If he was being honest, he kept them mostly for show, their gilded edges and soft leather bindings granting a serious look and an even more impressive smell to his digs. But enough about the books._

_His assistant stood tall with her back towards the door, and was tipping away from him trying to extend her reach. He took her in for several seconds, pale white slim legs stretching high, sky high. She was wearing a short black pleated skirt and from his angle he could almost see the crease where her flawless ass met the top of her creamy thighs._

Jessica's heart skipped a beat. He was taking a lot more time describing her than he normally did… a little apprehensive, she read on, quickly now trying to make sense of this chapter.

_She was still reaching up, running a finger along the volumes on the top shelf, looking for one in particular. Her arm stretched up above her head and from his place on the floor, Pepperwood could enjoy her body. Her tight black sweater moulded perfectly to her tight stomach and as she reached he could make out her ribcage and the mounds of her gorgeous breasts. Her slim, pale arm gracefully moved down the row of books. When she finally found the volume she wanted, drawing it down from the shelf, he was momentarily disappointed to lose his view._

_Then she turned around._

_Her sweater cut dangerously low down across her tits, and with the movement of stretching and reaching, the fabric had shifted. Her dark blue bra was sticking up slightly above the neckline, and her breasts had shifted too, now partially sticking out from the top of her sweater._

Jess, still in her seat, too shocked to stand up, scooted away from the computer screen. What the hell was she reading? Was he having some fun, transfixed with a fantasy, or was this going to turn into full blown…erotic fiction?! Trying to read faster, she scrolled down to the bottom of the first page.

_"Oh!" she expressed, surprised to see Pepperwood standing there. But she didn't fix her shirt. "Julius, I was hoping you could fill me in on our new case." I'll fill you in, Pepperwood thought, but kept that thought to himself. His cock had grown hard in his trousers at the sight of her long, naked legs and even harder at her exposed breasts, but thankfully his summer trench coat would keep that quiet too._

_His assistant sat perched at the edge of his desk, and crossed and uncrossed her legs slowly. Pepperwood happened to be looking. He saw that she was potentially not wearing any underwear. Encouraged, he shrugged off his trench coat. Maybe if she noticed his erection, it wouldn't be the worst thing ever._

_They seemed to be on the same page, as his sexy assistant extended her long, graceful arm and turned her wrist up, beconing him over with a confident clutch of her fingers. Pepperwood stepped closer, trying not to betray that anything was amiss. When he stopped a foot and half in front of her, she dropped her arm low and traced a finger up the side of his rock hard cock through his thin trousers. She paused at the top but did not stop touching him, rubbing the head of his dick with the pad of her thumb. "Or maybe," she whispered, "you could fill me in with something more personal."_

Jess's first reaction was, does that sentence even make sense?

Her second, and more lasting reaction was… WHAT THE HELL. Realizing how...personal this story was about to become, she closed the document and snapped his computer shut. Flushing now with embarrassment, she stood up and ran from his room, straight into hers.

Once inside she shut the door and started pacing. What the fuck what the FUCK? How could Nick be writing SMUT about them? Why was he doing this? Was he posting it online? Was he… sharing it with Schmidt and Winston? Were they laughing about it? After the revelation of the no-nail oath, she didn't know exactly where she stood with them or what else went on behind her back. How the hell could she have become a trampy character in his stories?

She heard the front door open and shut, and someone shuffle down the hall. It had to be Nick. Wow, Jess paused, feeling afraid. That was close. About the only thing worse than this would have been getting caught.

Jess looked down at her arms, at her body. From the sounds of the story, Nick had spent quite some time examining her. She felt really weird, and pretty angry.

But what could she even do about it? It wouldn't be easy to confront Nick, especially now that things were starting to get a little bit back to normal after he'd kissed her. Ugh, maybe he'd only kissed her to get more details for his writing porn. The thought made her sad.

She was really upset, and really embarrassed. I don't even know if I can tell Cece about this, Jess thought ruefully.

As the afternoon ticked by, she would try to work on other things, in her room with her door shut, but her mind just kept coming back to that story. As the shock wore off, it gave way to some surprising feelings. She expected to be so angry that she never wanted to talk to Nick again, and certainly not use his computer.

But by suppertime, the most urgent feeling she had was curiosity. What else happened in his latest chapter? The more she thought about it, she didn't even know for sure - sure enough to confront him - if the sexy woman in the story was her. She was determined to find out.


	2. Chapter 2

Jess endured a fairly quiet supper with Schmidt, lost in her own thoughts for most of it. While distractedly chewing her food, she realized she couldn't even ask Schmidt if this was normal, if he knew if other guys did this, because he would totally pick up that something had caused her to ask about such a weird scenario. I need guy friends who aren't my roommates, and not friends with these guys! Jess thought.

Jess decided that she'd reward herself with the story after she finished writing her next assignment instructions for her students (the file she'd foolishly started on Nick's computer - never again!). It's around 10pm and after she's poked her head out the door to ensure she's alone, she locks her door and opens the file. Skipping past what she's already read, she picks up the story on the second page.

_"I'm putty in your hands, girl," Pepperwood stated evenly to his assistant, who was eagerly stroking his prominent erection through his pants. He was surprised at her sexual attention. Unbeknownst to him though, Jessica Night had been fighting her attraction to the zombie detective for months, maybe even years. Her fantasies about him had grown all-consuming to the point that she had to act and she had to act fast. The desire was making her crazy. When he'd sent her home earlier in the afternoon, she realized all she could think about was him whether they were apart or together, and she knew tonight was the night she had to have him. The others could no longer compare. She just had to know what he felt like inside her tight pussy._

Whoa, Jess looked away from the screen again briefly. So it's definitely me, and it's definitely going to get dirty. Subconsciously, her right hand slipped down between her shorts and her panties, and without even being completely aware of it, she absentmindedly started stroking her clit through her underwear as she read on. The pad of her finger traced up and down over the fabric, feeling the warmth of her arousal.

_Sexy Jessica Night looked Julius straight in the eyes for the first time all night. Her bright blue eyes lined with black looked so hot and sensual. Her inviting red lips trembled slightly while she continued running a hand up and down his cock. Her other hand reached out and unfastened his belt, then undid the button and pulled down the zipper. His cock pushed out into this newly created space. She wasn't just teasing. Jessica Night, classy lady, was about to touch his dick! Pepperwood, although a smooth operator, was extremely excited about breaking this taboo with his own sidekick. Worried that he would say or do something to mess it up, he didn't speak, didn't move. He especially liked that she hadn't asked him if it was okay, didn't ask him if he wanted to do any of this. Somehow she knew Julius was hot to trot, and she was going to take what she wanted._

_Jessica slid off the desk and stepped towards him. She leaned a smooth, exposed thigh into his erection and trailed her hand up, stopping her circular rubbing she'd been doing for what felt like forever, but not breaking contact now that her warm thigh was in place, so dangerously close. She peeled off her tight black sweater with a swift motion, and then leaned forward to pull Nick's pants and boxers completely off, sliding them over his ass and then pulling them down in the front until they hit the floor._

_His dame hit the floor too._

Jess leaned back in her chair, realizing she was now touching herself to Nick's story. He had slipped up and called himself Nick instead of Julius. Knowing now that it was him who felt this way and that this wasn't just a writing exercise turned her on even more. She was applying a little bit of pressure to her clit, and after she scrolled to reveal a whole new page, she moved her left hand up to her breast and started feeling herself, imagining what Nick would feel, and how hard his cock would grow at the sight of her tits.

Reading on, she realized what a gift this invasive story was. If she ever wanted to make Nick cum hard, she would know exactly what he thought about.

_Gorgeous Jess Night was now looking up at him from the floor. Her blue eyes looked so innocent, but the dark eyelashes suggested she knew how to make men beg for release. Her hair tumbled down around her shoulders, slender yet strong. She was deliberately meeting his eye when she slipped her tongue out from between her lips, and slowly ran it over her plump, sensuous lips. She was so horny that even her own tongue on her lips felt good, anticipating the head of Julius's cock running along her lips soon. Reaching down between her legs, she started stroking her own slit while looking up at him. He wanted to groan, he wanted to fuck her right there, but she looked like she had a plan and he wanted even more to know what that was._

_Her lips full and moist, she reached out with her left hand and stroked Julius's naked cock. It was so hard she could see a vein bulging on the side, but other than that it was smooth. She couldn't wait to have it all inside her, so she slid her lips over the head and took him as deep as she could, her lips now brushing against his pubes. His full dick was all she'd ever wanted, and it filled her mouth. Mmmmm she moaned, causing his balls to tighten up. He thought he might cum any second and he fought for control._

Real-life Jess was rubbing herself more furiously now at the thought of Nick being so turned on. Her panties were wet now with her juices, and while vigorously rubbing her left nipple, she started fingering herself. Her small, delicate finger pierced the hot wetness of her cunt, in and out, and she imagined it was the much larger, harder, warmer penis of Nick Miller.

Outside, Nick returned early from his shift and was taken aback by the quietness of the loft. Thankful for a night to himself, he walked to his room, but paused when he heard moans. A slow smile spread over his face. Stopping in front of Jess's door, he could hear clothing rustling but heard no other presence. But he definitely heard the sounds of a woman confidently satisfying herself.

He turned his head, wondering what had happened that would get Jess so horny she had to get herself off. As much as he would love to enter her room and get her all the way there with his tongue, his head between her thighs, it seemed much safer to quietly continue on to his own room. A large part of him (really large, wink wink) wanted to eavesdrop until he heard her cum, but he knew himself enough to know that if he overheard that, it would torture him. He'd definitely be liable to break down the door and try to join in. That, or she'd likely hear him sneaking away once she stopped..whatever noises Jess made during orgasm.

Sighing to himself, he quietly opened his door and laid on his bed. Without even really thinking about it he unzipped his pants. Nick lazily stroked his cock, thinking of her, too tired to put much thought into elaborate Pepperwood & Night scenarios, his new favourite fantasy. Besides, for tonight he could have a new real life fantasy. She was 20 feet away touching herself, bringing herself to orgasm. Horny and sexy enough to have to cum tonight, alone.

I wonder who she's thinking about… I wonder if she's watching porn - what kind? - or if she uses a vibrator? At the thought of Jess with a really big dildo, Nick almost laughed and went back to imagining her lying in her bed, just touching herself with her own hands, imagining him fucking her. That's what he'd like to think anyway. His hand tightened on his erection and he fell into his natural habit of stroking up and down quickly just under the rim of his dick. It wasn't long until he had turned his head and was groaning into his sheets as a hot length of cum shot from his cock.

Mmm, he thought, satisfied, once his thoughts came back to earth. In his post-orgasm haze he wondered when he would ever stop fantasizing about her. It was always her, these days, either real her or his fictional sidekick. He didn't feel quite so bad when it was Jessica Night. He did dirtier things to her. He happily indulged his fantasy that she was not so far away, imagining him doing those dirty things to her.. or maybe imagining herself doing things to him.

Across the hall, Jess was trying hard now not to cum before finishing the story. She didn't know how much she'd care to read it once she'd finished. In the story, fictional Jess gave "Julius Pepperwood" a very long, detailed blow job. Her pussy was tight now though and aching for her body to let her orgasm. She read on.

_She explored every area, sucking his extremely hard dick. Though fighting for control and still uncertain despite her obvious lust for him, Julius eventually allowed himself to express some pleasure at the situation, groaning gruffly as Jess stroked his balls with her thumb. While she enthusiastically took him deeper into her throat and faster, and as the head of his cock swelled filling her throat even more, he pulled her long hair between his hands. Jess Night was extremely turned on by Julius's huge, glistening dick, and by blowing him. She had been touching herself the whole time she tended to him, now sucking him with just her mouth and feeling her own breasts through her bright blue bra. His assistant's left hand continued to fondle her own breasts as she reached her right hand out between Pepperwood's legs, stroking his inner thighs while she continued to lick his cock hands-free. He shuddered at her touch. His cock was so hard that it just stuck straight out from his body, barely moving while she plunged it into and out of her mouth. As Julius's cock jerked with arousal, Jess finally let herself cum from her own touch. _

_But she didn't want him to get off like this. As much as she had craved his dick in her mouth, she craved other things too. Without warning, less than a second after finishing her orgasm and the primal cries that came with it, Jess stood up and kissed Julius's neck, interrupting her own kiss with short but firm bites. She bit him all over, his chest, his nipples, his shoulders, his lips, his earlobes, while he slowly pumped his own dick. Her hair trailed over his skin as she nipped at different areas of his body, taking his arousal to an incredible new height. _

_When Jess looked down and saw Julius's own rough hand choking around his hot, glistening cock, she moaned. She couldn't look away. Backing up a few steps, she sat her ass back down on the edge of the desk, staring at Julius and watching his movements, transfixed. She looked incredible. Her chest had flushed after her own orgasm, and her nipples were peeking out, hard, over her blue bra. Apart from that her skin was flawless and pale. Her stomach looked irresistible to Julius, especially her tiny belly button, before the mysteries of the rest of her body were covered by her short black pleated skirt._

_Groaning, he could handle her beauty and seduction no more. He stepped up in front of her, taking control, causing her to lean back slightly. Pepperwood raised a knee up on the desk while standing with his other leg on the floor, half straddling her, which forced her to lean back even further. Reaching down with his left hand, he ran a single strong finger up her, naked under her skirt. He stroked her from tight asshole to clit, making sure to dip his finger in her cunt hard as he traced this line, over and over again. Jess writhed into his hand and stared wide-eyed at his cock, being pumped so hard right in front of her. She was so turned on that this time when his finger pushed into her, her pussy walls tightened and she started to come. He slipped another finger inside and curled his fingers up, stroking her inside while she came so hard. Just as she was coming down after the last waves of an extended orgasm, his balls tightened up and with a satisfied moan he shot his hot sticky load all over her torso, making sure to hit as much of her beautiful stomach as possible. It hadn't been her plan - she'd wanted to fuck him hard on the desk. But as soon as his hot cum hit her skin, she realized she would have a new fantasy. She wanted Pepperwood's juices everywhere._

Barely able to read this last paragraph through her arousal Jess finally allowed herself, the reader, to cum. She couldn't stop thinking about how turned on Nick must've been when he wrote this. It was kind of sweet. Closing the file, and her computer, she tried to put it out of her mind while she slept, unaware that Nick had even come home.


	3. Chapter 3

The days that followed had Jess very confused. She and Nick still didn't really talk about what if anything was going on with them. Jess couldn't decide if it helped or not that she knew about his written fantasies.

It certainly would lead to some interesting discussions if she ever brought it up. If we ever talk about how we feel again! Jess thought to herself, slightly frustrated.

Jess realized that she was having trouble deciding what to do on her own. It was time to fill Cece in, a little. Partially to protect Nick, she decided in advance she wouldn't tell Cece everything. Fantasies were personal, and Nick's were very detailed. Even though he projected a tough, too cool to care attitude, she knew it would hurt him if others knew about the story. (This led her to more questions, such as how bad her own invasion of his privacy had been... and, in contrast, if there were more stories on his computer.)

Cece and Jess walked and chatted, but it took Jess a while to get up the courage. To be honest, she was often distracted as segments of Nick's erotic story drifted through her mind. She'd fantasized about kissing him since True American, definitely. A lot. But the more she thought about it, she was mostly imagining the feelings. The sensation of his warm, just-the-right-size body pressed against her. She'd had sexual thoughts about him from time to time, but it never got as detailed as imagining him jerking off over her body and coming on her. She definitely didn't mind these new possibilities to think about, but it was taking a little getting used to. It brought their changing relationship, from roommates to close friends to whatever was next, into graphic relief.

Over late-afternoon drinks and appetizers she finally revealed the underlying reason she'd called Cece. "So...I have pretty solid proof that Nick wants to have sex with me." Cece tried to keep chewing her salad but her mouth wouldn't quite close enough each time. She eventually swallowed and smirked. "Proof? Did you finally feel his boner?" She teased her friend, smizing.

Jess rolled her eyes and pressed on. "I guess I'm still in the same predicament. He's so important to me. I want to know him when I'm 45. And if we date now, well, unless we get married, we break up. I don't talk to Spencer or Russell and if I hadn't worked with Paul I doubt I'd talk to him either. The stakes just seem so high."

Cece became serious. She spoke slowly, with great care. "Jess, I usually give you pretty good advice. But with you and Nick, I am just as lost as you. This," she said, pointing her fork at Jess, "is why I don't date friends, I date strangers!"

Jess smiled sadly. Cece also didn't really have guy friends, except through Jess. But she knew what she meant. It was comforting even just to know that the solution wasn't obvious to everyone but her. Clearly, if Nick wanted so badly to sleep with her but hadn't made another move or even addressed it, he was having his own internal struggle. She couldn't even begin to guess what pros and cons he was weighing, and vowed to keep any assumptions about his feelings out of it. And if Cece didn't know what to tell her, well, that left her.

After some moments of reflective silence, Jess piped up again. "From how much I've thought about the kiss I know there is sexual chemistry there. We're definitely sometimes attracted to each other." She affirmed, still mulling things over. "But in order to risk our entire friendship and living situation... I think I need more than that."

Cece sat back and adjusted her thinking. This made sense. For her, to sleep with a stranger because they had chemistry, well, she didn't really have anything to lose. But for Jess, doing anything more with Nick had inherent real risks.

"Okay, so what I'm hearing is that you would only be willing to risk what you have now if you really thought it would work out. So what would that look like for you, Jess?"

She was still thinking about what that might be. "Well, the sex is definitely part of it but based on the kiss let's say that won't be a problem like it has been with my exes." (She also had her newfound extensive knowledge of his fantasies, so yup, no problems there.) "I guess the rest is companionship and support...or love..." she continued.

"Well, you guys seem to enjoy spending time together, so that's the companionship. And he's done a lot for you as a friend, between the dresser and being there for you when you lost your job." Jess nodded at Cece's truthful summary.

"Okay, so this isn't the craziest idea. Let's say we do talk and decide to date. But what does that end up looking like, with our living situation?" Jess would clear one hurdle mentally, and but there was always another one waiting. And despite this serious conversation, a small part of her brain was still processing _Pepperwood's glistening cock_.

"Let's put a positive spin on it. You already live together. But you don't live _alone_ together, so it's not quite as intense."

Jess picked up Cece's thread. "Yeah, okay. So if I wanted to watch a movie that he didn't, I could still do my own things, but not worry too much that I'm being selfish because we would still have plenty of down-time together, like breakfast and even cleaning up or doing loft errands."

Cece nodded but added "I wouldn't even think about the domestic stuff too much yet. Think about your dates, your hobbies."

"I guess if we were dating we would try to get involved in each others' interests a little more... just like we're doing as friends."

"Yeah..." Cece reflected. "There's a couple of big areas that I wonder about, if you want this to last. What about your...different personalities? And your life goals?"

Leave it to Cece to drop the big bombs. I guess that's a fair question, Jess thought, especially since Cece had these things on her mind while trying to find a marriage partner herself.

"Well, how do you handle those questions, with your suitors?" Jess grinned, emphasizing the last word.

Cece took a moment to answer, sipping on her drink. "Because of the very upfront nature of it, the life goals stuff comes out pretty immediately. I think that might be a hard area for you guys." She smiled softly at her friend. "I know you're not the happiest with your work situation this year, but that could be an advantage too. You might both be looking to make a change at the same time. Despite what he says, Nick is probably a little self-conscious about where his life is heading right now. If you were all set in your career, he'd probably feel bad. But if you guys are both looking to make a change, you could make it together. Go back to school, look into different fields, anything." She paused, and looked directly at Jess. "The biggest question I have about him is, what does he actually want out of life? Even if you guys have a blast together, it is just about time to start getting serious about the future. If he has the ambition and the dedication, I don't think it matters so much where he is this second. It's about where he wants to be and how he plans to get there."

Jess turned her glass in her hand, around and around again on the table, comparing Cece's words to her own feelings. Ugh. She was getting there, slowly, but it was a long road. And what did she have? On the one hand, she had Nick's incredibly detailed and dirty fantasies about what Julius Pepperwood might do to Jessica Night. The sidekick in the story had her body but that was about all she had found out. At the worst, Nick is a fairly nice normal guy who maybe really wants her body and maybe just wants to live with his best friends and serve drinks until whenever. And if that was all there was to it, this wouldn't be worth it.

She couldn't let herself think about the best-case scenario, knowing it was so unlikely to be true.

But she knew enough about people to hope that the real truth was somewhere in the middle. So maybe all Nick wanted out of life was a good time, but he liked her. Or maybe he just wanted her body, but harboured ambitions to do more in the world than he was at the moment. She did know, for sure, that he cared about her as a friend. Convinced, finally, she let her full heart's feelings roam all the way through her body, quieting her mind, tingling between her legs, and tugging at her lips.

Cece took in her friend's changed posture at the table. Shoulders no longer hunched high, body no longer fidgeting. Just like when she'd decided to move to LA, to do her master's, to apply for her first job at the school - she could see that her friend had made up her mind, and to that, Cece lifted her drink and offered a silent toast.

Jess lifted her own glass and they both smirked over their clinking glasses. Jess's eyes had a deviousness to them. Cece couldn't wait to find out what would happen next. When your best friend finds love, it's even better than when you do, she thought to herself excitedly as she turned to admire the late evening sun.


	4. Chapter 4

Jess had opened that file on her computer way too many times since first transferring it. She was reading it every night before going to sleep. Yes, she was getting off on it every night too. She analyzed every word.

She also tried to pay attention to Nick in real life. They still got a little cagey when they got too close to each other. When his leg brushed against hers at the table or he leaned over to help her with something, her senses heightened. She found herself holding her breath, pulse pounding in her ears as she noticed something new about him every time he got too close. How kissable the skin on his neck looked, especially where he had a bulgy vein. And that only made her think about the other place where he might have a bulgy vein.

And yet, having resolved (without speaking about it) to try to get back to normal, they hadn't discussed anything. She was tired of feeling confused and uncertain. She wanted to confront him, but in a way that would ensure he couldn't panic moonwalk away.

The week that she made up her mind, she first of all made sure she had all her supplies. And then she waited. Waited for the perfect opportunity. After having made up her mind, the waiting was excruciating. The days seemed to pass so slowly, and if she missed an opportunity, it drove her crazy with doubt and regret.

There was one night when she thought it would all work out, and then Schmidt came home and wanted to try a new recipe with her. Another night, it looked like the pieces were falling into place, until Winston actually had the night off and got Nick out to play basketball. As the days passed though her determination only grew. This was the only way to figure out what was going on between them, what they both really wanted. Anything else up to this point hadn't worked at all.

* * *

Nick opened the refrigerator door and saw nothing that interested him in the slightest. "Guys," he called out, "what's everyone doing for supper?" "I'm meeting Daisy!" Winston called back excitedly, doing his mojo man dance with a huge grin on his face. Schmidt looked up from his computer. "I'm heading out for another baby shower - hopefully transitioning into a babe shower! Shower with some babes?" He reached up and pantomimed being in the shower with a girl, which bore a strong resemblance to pole dancing. "Schmidt, I might be wrong but I think they only do pole-dancing lessons for bachelorette parties, and I don't see you ever being invited to one of those." Winston even stopped his dance to shudder at the thought.

Well, they're out, he thought, which leaves only Jess. She hadn't answered. He knocked on the frame of her open door and poked his head around the corner. "Jess? Supper plans?" She was sitting on her bed and looked like she was working. She was forming silent words with her mouth while reading a paper. "Hmm?" she looked up at him and raised her eyebrows over her dark-rimmed glasses.

"There's nothing good in the fridge, I'm going to pick something up. Do you want any?" He explained, patiently. She seemed so distracted.

"Oh, yeah that would be great, thanks! I'm pretty hungry, how long will you be?" Nick squinted at her alarm clock. "I think they'll be ready in half an hour, so I can be back here by 7, will you last until then?" he grinned at her. Such a girl, he thought.

Jess nodded, looking back to her paper. "Thanks Nick, yup I can hang on until then." He shuffled out of the loft to pick up their meal.

* * *

In the minutes that followed, Jess tried not to stress too much until both Winston and Schmidt had also poked their heads around her door to say goodbye. She'd overheard them saying they would be out but wanted to play it cool, which was pretty hard for her. Finally, the stars lined up. As soon as she heard the ding of the elevator from the hallway, confirming that the guys had left and wouldn't be back, she pulled her things from their various hiding places and got to work.

40 minutes later, Nick hurried back into the apartment with 2 bags of takeout. He hadn't planned to have a meal alone with Jess but he wasn't disappointed at the way it had turned out. He smiled, wondering how supper would go. They were doing pretty well with being normal around each other, but it was still kind of exciting to him. He expected a hungry Jess to be waiting at the table for him, maybe with a couple of drinks ready, but there was no one there.

"Jess?" he called out. He set the food on the table and put his keys away by the door. Still not hearing anything he wondered what was up. "Come on Jess, quit playing around, we're both hungry and you knew I was coming back!" He was a little exasperated. His prettiest roommate could be a bit flighty sometimes, but to go from being so serious grading papers to having seemingly disappeared...?

Maybe Sam called, he thought, dejectedly, as he turned the handle on his door, no sign of Jess in her room or anywhere else.

When he stepped in his room, his eyes automatically locked on the human figure. At eye level ahead of him, standing on his desk, were a tall, naked pair of legs. He drew his breath in sharply but tried to betray no other reaction. He followed the legs up to see Jess standing there, her back to him as she dusted the top of his window frame.

He was frozen in place as he looked over her body. She was wearing shiny black heels, very professional, the type and height he had seen on the toughest female lawyers. But unlike them, she wore no hose, no pantsuit. Her slim legs were nude, starting with her skinny ankles, her perfect calves, and god those thighs...

Glancing up, he saw that she did have clothes on. She was wearing a very short, school-girl style black skirt, the sight of which was causing some problems in his pants. With her standing up so high and leaning away from him, he could almost see the curve of her ass cheeks, but not quite. Even just thinking about her pert ass, his erection grew.

Above the small skirt was a tight black sweater. It clung to her waist, the tight feeling of which he had memorized after their possibly ill-advised kiss. Her long dark hair looked extra fluffy and gorgeous, falling around her shoulders and back, begging to be stroked. And her arms reached up even higher, just lightly dusting the top of his window frame. His eyes paused on her ribcage. Though her tight body was covered by the sweater, it hugged her so closely it wasn't hard to imagine the perfection underneath. He wanted to grab her there, beneath her breasts, and pull her to him.

Once he got over the shock, he thought - what the HELL is she doing?

Just as he was about to speak, she slowly spun on her heels. He stared at her, mouth agape, still unable to move or respond. Now he was stuck looking at her gorgeous flushed face, eyes shining. Casting his eyes downward just a bit, another shock.

Her fucking tits.

Jess's tight black sweater was too small, and it did not at all cover her boobs, or even her bra. A deep navy-blue bra peeked out over the top of the neckline, but what caused his breath to catch in his throat was the sight of her pale breasts, the top of her mounds unconstrained by the bra, pushed up so high on her chest.

Confusion hit his body with full force. She looked incredible, and for once not cute or not or relaxed but purely sexual, and he just wanted to pounce on her and touch her everywhere with his fingers, his face, his lips, his cock. But why was she up there, on his desk...

* * *

Jess had never been this nervous in her life. What had seemed like a brilliant idea - bringing his fantasy to life - now seemed totally crazy. But she made up her mind while she stood on his desk in her heels, patiently waiting for his return. She knew she'd change her mind, but that she shouldn't, so she wasn't going to move. Now that she was up here, in this, she was going for it, no matter how many times she thought she might chicken out. It was definitely crazy, but she hoped it was the right kind of crazy for Nick.

When she heard him enter the apartment, she assumed her position. She parted her legs slightly, hoping her stance and her short skirt would draw his eyes to her thighs and her ass. The cool air of his room hit her already moist pussy, causing her to shudder a bit, and moisten more.

She was determined that this was going to turn out a million times better than when she had tried to stage a sexy surprise for Spencer. She reached up and practiced dusting his window, the most analogous activity she could find to his fantasy of perusing Pepperwood's office bookshelves. She'd memorized everything in the "chapter" she'd read, all her dialogue, all their actions, and she was so excited to live out Nick's fantasy for him. This would show him that it was okay, his feelings, her feelings, what they wanted to do to each other and be together, it was all okay.

Even though her back was to him, she felt his presence when he entered the room, heard his intake of breath. She tensed a little bit but tried not to let it show. The fantasy was that this was perfectly normal.

The worst part was him not saying anything. It threw her into complete internal chaos. She was more than putting herself out there for him, but she had no way to know right now how he felt. After a few seconds of pretending to dust, she turned to face him, putting on her brightest smile. As nervous and terrified as she felt, she was damn excited too. And standing up there in her sexy outfit, without any panties, well, she was aroused already.

But when her eyes met his, she saw recognition flash across his face, his jaw clench along with his fists, and then brows furrow in anger.


	5. Chapter 5

Nick stared up at her, standing on his desk in her stilettos, pale legs launching her high above him.

She was fucking with him. Somehow, she'd found out, and she was here to make him pay. She smiled down at him, so confident. Bitch, he thought, staring her right back while he slowly inched himself away. Fuck, did she tell anyone? His stomach churned with shame and anger as he tried to process how his best friend could do this to him.

Jess's face fell as she noticed him backing away. "Nick, wait!" she called out, lowering herself carefully to the desk, using one hand on its surface for balance.

Fuck, Nick thought, taking in the sight of her lean legs. Her skirt shifted upwards as she bent over, trying to get down safely from the height. She looks like a fucking porn star, he couldn't help but think, as her raven hair tumled down. She didn't have enough hands to both balance and cover herself, and he caught a flash of an ass cheek as she dismounted. His erection grew, confusing his feelings even more. He set his face in anger.

He moved slowly due to shock, but it seemed to speed her up once she got down from the desk. Within a second she was standing in front of him, face to face thanks to her heels. She reached out to grab his arm, a motion that finally got a reaction out of him.

Nick grabbed her upper arms forcefully and stepped into her. He turned and pushed her against the wall, pinning her there. He still didn't say a word, so angry, so betrayed. Where would he start?

"Nick, I'm sorry, I found it by accident." She admitted, words coming out jerkily as she struggled to breathe normally. "I just wanted to do what you wanted, to show you that it was okay." He loosened his grip as he processed what she was saying.

"Jess..." he didn't know, what to tell her, what to do, anything. Studying her in his arms, he saw that her chest was heaving, her flushed breasts still exposed over her sweater. Her arms were pinned beside her, but they were standing so close that she could reach out and slide her fingers between his stomach and the waistband of his pants. She cocked her head and looked at him, smiling.

"I want you, Nick. I want to feel what it's like, for you to do what you want with me."

At those words, words he'd never thought he'd hear, he released his grip on her arms and stood there in defeat. He had so many questions. But here she is, standing in front of him, so fucking sexed up, and telling him she wants him.

He still eyed her suspiciously. "You're not trying to get revenge on me?" He asked, squinting.

"Nick, no, I just finally wanted to go for this and doing what I already knew you wanted seemed like the easiest way." She slid her hand down farther, breaching the elastic barrier of the top of his boxers, her cool fingers finding the throbbing head of his cock. He was still wary, but she seemed determined. Go for it, you idiot.

He smiled. "Alright then... well in the story, I think you stroke me through my pants, you eager little minx!" he teased, catching her arm with his warm fingers. "But," he continued, "if we're going to do this...we should just do our own thing, don't follow the script." he suggested, a part of his brain piecing together what he had seen her doing earlier. She hadn't been grading papers, she'd been studying his fantasy. Maybe this is what she meant by nerdy weird sex, he thought.

She was looking at his face, not just his eyes or his lips, but searching his whole face for clues about how he might feel. His suggestion made sense, they should just do what they felt like. But she had one reservation. Nodding slowly while she tentatively explored his hard on, she countered with a suggestion of her own. "Um, Nick, can we stay in character this time? Just in case..."

Her brief sentence told him so much. His heart lept in his body and he couldn't help but smile at this devious girl. This time, he thought to himself. She wants a next time already. But she wants us to role play, just in case... if it's all a horrible mistake, it wasn't Jess Day and Nick Miller, it was Julius Pepperwood and Jessica Night. Genius, he thought to himself, and I wish I'd thought of it.

"All right _Jessica Night_, I guess I just have to say, I'm shocked that you came back to my office tonight."

Getting into it, she replied. "Don't be so surprised, Julius, you know I've wanted to do this for a...long..." she paused while she stroked the full length of his erection with her other hand, "time." He fought off a shudder and a small moan and stared at her wide-eyed as she undid his pants and pushed them down to the floor. She was getting ready to kneel down when he reached forward and caught the bottom of her sweater in both hands, curling his fingertips up underneath and brushing her smooth skin. He gently tugged her closer.

Brushing his nose against hers for just a fraction of a second, savouring the moment before committing completely...he then lowered his lips to hers, warm and powerful, kissing her with everything he had. One of her hands gripped his cock while the other snaked up around his neck, pulling him in deeper. He slowly raised his arms, pulling off her shirt but not being willing just yet to break from her mouth. As the sweater got stuck above her breasts, they pulled apart. She let go and removed it herself, then locked herself right back into place, prying his mouth open with her tongue.

Her feelings were warm and electric. This was already the best sex she'd ever had. She felt naughty, fun, flirty, competent for once, sensual, and just right.

He nipped at her tongue, forcefully closed his lips and placed one more sealing kiss on her mouth. Then he leaned back, catching her hands in his and rocking on his heels. He still had his shirt on but his pants and underwear were around his ankles. Looking down, he saw her sexy black heels standing tall amidst the pile of clothes. Her short black skirt that was as effective as lingerie, looking even better now that she was naked from the waist up. He smiled at the sight of her bare stomach. She was quivering, just barely perceptibly. And then her gorgeous face, her lips full from kissing him and slightly irritated by his scruff already.

She leaned back into him as her fingers worked at the buttons on his shirt.

"You never kissed me in the story." She accused playfully. Where did this confidence come from?

He circled his arms around her lightly.

"I could never write that." He replied with a grin. "Before we kissed, I couldn't even imagine it, it was just too hot for me." Said the man who had put his thoughts about coming on her to paper. "And after..." his dark eyes met hers and everything turned serious. Shaking his head slightly he admitted, "I couldn't have captured it again." He didn't wait for her next questions, her reaction. Just like in the story, she wasn't asking him if it was okay. She knew it was okay. But he had to be sure. "Jess, you know what we're doing, right? You're okay with...whatever happens?"

She didn't answer him with words, she just used the last of her height advantage to slip his shirt off his shoulders. She met his eyes one last time, then stepped out of her heels one by one and pulled him backwards to his bed.


End file.
